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$240+ Cheap flights from Durango (DRO) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
DRO — CHI
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
1 adult, Economy
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Cheap flight deals from Durango to Chicago

Cheapest flights from Durango to Chicago
Explore the most affordable flight options available from Durango to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.

This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:05 pm
DRO
-
ORD
1 stop5h 39m
United Airlines
Sun 7/55:00 am
ORD
-
DRO
1 stop5h 33m
United Airlines
Deal found 5/18$290
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:06 pm
DRO
-
ORD
1 stop6h 33m
American Airlines
Tue 6/235:00 am
ORD
-
DRO
1 stop7h 18m
American Airlines
Deal found 5/16$324
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:05 pm
DRO
-
ORD
1 stop5h 39m
United Airlines
Sun 7/55:00 am
ORD
-
DRO
1 stop5h 33m
United Airlines
Deal found 5/19$344
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:07 pm
DRO
-
ORD
1 stop5h 59m
American Airlines
Mon 9/144:09 pm
ORD
-
DRO
1 stop6h 04m
American Airlines
Deal found 5/20$352
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:00 am
DRO
-
ORD
1 stop8h 00m
American Airlines
Sun 11/1512:10 pm
ORD
-
DRO
1 stop7h 12m
American Airlines
Deal found 5/16$358
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:05 pm
DRO
-
ORD
1 stop5h 39m
United Airlines
Tue 6/305:00 am
ORD
-
DRO
1 stop5h 33m
United Airlines
Deal found 5/20$370
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:18 am
DRO
-
ORD
1 stop6h 14m
United Airlines
Wed 9/95:00 am
ORD
-
DRO
1 stop5h 36m
United Airlines
Deal found 5/20$378
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:06 pm
DRO
-
ORD
1 stop6h 33m
American Airlines
Wed 7/85:00 am
ORD
-
DRO
1 stop5h 51m
American Airlines
Deal found 5/20$379
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:15 am
DRO
-
ORD
1 stop5h 08m
United Airlines
Sun 6/215:00 am
ORD
-
DRO
1 stop5h 33m
United Airlines
Deal found 5/18$388

Find flight deals from Durango to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Durango (DRO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$290
(United Airlines)

One-way from

$240
(United Airlines)

Popular in

May

Cheapest in

January

Average price

$503
Provider with most accurate pricing for Durango La Plata County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Durango La Plata County-Chicago (CHI) flights.
Search Deals
From Durango La Plata County to Chicago (CHI)
Search Deals
One-way flight from Durango La Plata County to Chicago (CHI)
Search Deals
High demand for flights, 10% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Durango to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 21, 2026.
Use the filters below to find and compare flights from Durango to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Fri 7/3

6:05 pm-12:44 am

1 stop5h 39m

Chicago O'Hare Intl

Sun 7/5

5:00 am-9:33 am

1 stop5h 33m

$290

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Fri 7/24

6:05 pm-12:44 am

1 stop5h 39m

Chicago O'Hare Intl

Sun 7/26

5:00 am-9:33 am

1 stop5h 33m

$344

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Wed 9/9

12:43 pm-10:18 pm

1 stop8h 35m

Chicago O'Hare Intl

Mon 9/14

5:00 am-12:02 pm

1 stop8h 02m

$352

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 10/29

7:00 am-4:00 pm

1 stop8h 00m

Chicago O'Hare Intl

Sun 11/15

12:10 pm-6:22 pm

1 stop7h 12m

$358

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 10/29

6:00 pm-11:57 pm

1 stop4h 57m

Chicago O'Hare Intl

Sun 11/15

5:00 am-10:46 am

1 stop6h 46m

$378
Quickest round-trip

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Mon 6/15

5:15 am-11:23 am

1 stop5h 08m

Chicago O'Hare Intl

Sun 6/21

5:00 am-9:33 am

1 stop5h 33m

$388

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Fri 6/19

1:30 pm-8:30 pm

1 stop6h 00m

Chicago O'Hare Intl

Sun 6/21

5:00 am-9:33 am

1 stop5h 33m

$394

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 6/18

5:15 am-11:23 am

1 stop5h 08m

Chicago O'Hare Intl

Sun 6/21

5:00 am-9:33 am

1 stop5h 33m

$419
Cheapest one-way

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Fri 6/19

6:05 pm-12:44 am

1 stop5h 39m

$240

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 6/4

5:06 pm-12:44 am

1 stop6h 38m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/19

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

Compare providers for flights from Durango to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Durango to Chicago in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Durango-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Durango-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Durango-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Durango-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Durango-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Durango to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Durango with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Durango to Chicago

What is the cheapest month to book a flight from Durango to Chicago?

Currently, November is the cheapest month in which you can book a flight from Durango to Chicago (average of $213). Flying from Durango to Chicago in May is currently the most expensive (average of $380). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Durango to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 21, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Durango to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,748 reviews

Comfort

7.3

Boarding

7.7

Overall

7.4

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,748 reviews
United Airlines
7.4
Good
9,748 reviews

Comfort

7.3

Boarding

7.7

Overall

7.4

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.1
Good
11,641 reviews
United Airlines
7.4
Good
9,748 reviews

Comfort

7.3

Boarding

7.7

Overall

7.4

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

Related info for your journey

Find useful and relevant information for your journey from Durango to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Durango to Chicago?

    Most people fly from Durango La Plata County (DRO) if they book a flight from Durango to Chicago. On average, La Plata County has 0 outbound flights to Chicago per day from 2 airlines. Durango La Plata County is conveniently located just 11.0 mi from Durango’s city center.

  • How long is the flight from Durango to Chicago?

    For as low as $290, United Airlines can have you in Chicago from Durango in 5h 39m. The distance from Durango to Chicago is about 1105 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Durango to Chicago round-trip?

    United Airlines, at $248, was found to be the cheapest airline from Durango to Chicago. An alternate airline flying to your destination would be American Airlines. United Airlines is 40% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Durango to Chicago that include hotel bookings?

    Yes. In addition to deals on Durango to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Durango to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Durango to Chicago.

  • Can I find deals for business class flights from Durango to Chicago?

    Yes. Cheapflights offers flight deals from Durango to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Durango to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Durango to Chicago (average of $213). Flying from Durango to Chicago in May is currently the most expensive (average of $380). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 2 airlines flying from Durango to Chicago

Discover the top 2 airlines that operate flights from Durango to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$248Average$488FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$318Average$428FlexibilityNo cancel feeOn-time71%

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